Hydrochloric Acid → 2-Methoxy-5-(1,1,2,2,2-pentafluoroethyl)benzaldehyde

HRID 2269260Notes

Reaction equation

HRID 2269260 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])=[CH:5][C:4]=1[CH:16]1OCCC[O:17]1.Cl>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:14])([F:15])[C:10]([F:11])([F:12])[F:13])=[CH:5][C:4]=1[CH:16]=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18677628HCID 18677628, compound

Product 1

HCID 186776122-Methoxy-5-(1,1,2,2,2-pentafluoroethyl)benzaldehydeYield 33.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of Compound 39 (1.0 g) in acetone (30 ml) was added conc. HCl (4 ml) at room temperature. The reaction mixture was stirred at room temperature for 5 h. The solvent was evaporated in vacuo and the residue was extracted with ether. The combined solution was washed with sat. NaHCO3 aq., and brine, dried(MgSO4) and concentrated in vacuo to give crude product (790 mg) as a yellow solid. The crude product was purified by column chromatography on silica gel with hexane-isopropyl ether(10:1-3:1) to give Compound 40 (275 mg) as a pale yellow solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionthe residue was extracted with ether
  3. washThe combined solution was washed with sat. NaHCO3 aq., and brine, dried(MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give crude product (790 mg) as a yellow solid
  6. customThe crude product was purified by column chromatography on silica gel with hexane-isopropyl ether(10:1-3:1)

Sources & evidence

ORD record
ord-759deea35bcc45adbf4024a3b051eb64
Source dataset
uspto-grants-2001_12
Patent number
US06329396B1

Reaction notes

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